NP-MRD: Showing NP-Card for (1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate (NP0318887)

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Record Information

Version

2.0

Created at

2022-09-11 19:38:14 UTC

Updated at

2022-09-11 19:38:14 UTC

NP-MRD ID

NP0318887

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate

Description

(17S)-1alpha,7alpha,11beta-Trisacetoxy-14beta,15beta:21,23-Diepoxy-4,17-dihydroxy-13alpha-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-Disecodammara-20,22-diene-3,16-dioic acid 3,4:16,17-Bislactone belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate is found in Cedrela odorata. Based on a literature review very few articles have been published on (17S)-1alpha,7alpha,11beta-Trisacetoxy-14beta,15beta:21,23-Diepoxy-4,17-dihydroxy-13alpha-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-Disecodammara-20,22-diene-3,16-dioic acid 3,4:16,17-Bislactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221382D          

 44 49  0  0  1  0            999 V2000
    2.0961   -2.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043   -2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518   -2.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -1.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5 44  1  0  0  0  0
 21 44  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309112221382D          

 44 49  0  0  1  0            999 V2000
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    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2508    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0442    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050    2.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575    3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132    3.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144   -2.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 37 42  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  1  1  0  0  0
 44 42  1  1  0  0  0
  5 44  1  0  0  0  0
 21 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318887

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]23[C@]2(C)[C@@H](C[C@@H]3[C@@](C)([C@@H]12)[C@H](CC(=O)OC3(C)C)OC(C)=O)OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O12/c1-15(33)39-19-13-29(6)25(18-9-10-38-14-18)42-27(37)26-32(29,44-26)31(8)22(41-17(3)35)11-20-28(4,5)43-23(36)12-21(40-16(2)34)30(20,7)24(19)31/h9-10,14,19-22,24-26H,11-13H2,1-8H3/t19-,20-,21-,22+,24+,25-,26+,29-,30+,31+,32+/m0/s1

> <INCHI_KEY>
LLKSEVKQBGUFFZ-DMULSHIBSA-N

> <FORMULA>
C32H40O12

> <MOLECULAR_WEIGHT>
616.66

> <EXACT_MASS>
616.251976728

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.21934474041234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,7R,8S,10S,11R,12R,13S,18R,20R)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icosan-10-yl acetate

> <JCHEM_LOGP>
2.027342453666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8725941870144447

> <JCHEM_POLAR_SURFACE_AREA>
157.17000000000002

> <JCHEM_REFRACTIVITY>
146.32390000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7R,8S,10S,11R,12R,13S,18R,20R)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icosan-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.913  -4.147   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.421  -3.838   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.443  -4.990   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.908  -2.377   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.119  -4.157   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.342  -4.644   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.201   2.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.816   4.001   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.303   5.462   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.281   6.614   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.811   5.771   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.814   2.536   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.975   3.828   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.887   3.641   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.130   1.737   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.326   0.209   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.787  -0.278   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.253  -0.896   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.720  -0.747   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.921  -2.063   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.661  -3.413   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.200  -3.448   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.307  -4.912   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   44                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    9   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18    7   21                                             
CONECT   21   20   22   23   44                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   42                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37   29   43   44                                             
CONECT   43   42                                                            
CONECT   44   42    5   21                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Value	Source
(17S)-1a,7a,11b-Trisacetoxy-14b,15beta:21,23-diepoxy-4,17-dihydroxy-13a-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-disecodammara-20,22-diene-3,16-dioate 3,4:16,17-bislactone	Generator
(17S)-1a,7a,11b-Trisacetoxy-14b,15beta:21,23-diepoxy-4,17-dihydroxy-13a-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-disecodammara-20,22-diene-3,16-dioic acid 3,4:16,17-bislactone	Generator
(17S)-1alpha,7alpha,11beta-Trisacetoxy-14beta,15beta:21,23-diepoxy-4,17-dihydroxy-13alpha-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-disecodammara-20,22-diene-3,16-dioate 3,4:16,17-bislactone	Generator
(17S)-1Α,7α,11β-trisacetoxy-14β,15beta:21,23-diepoxy-4,17-dihydroxy-13α-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-disecodammara-20,22-diene-3,16-dioate 3,4:16,17-bislactone	Generator
(17S)-1Α,7α,11β-trisacetoxy-14β,15beta:21,23-diepoxy-4,17-dihydroxy-13α-methyl-23-des(2-methylpropyl)-30-nor-3,4:16,17-disecodammara-20,22-diene-3,16-dioic acid 3,4:16,17-bislactone	Generator

Chemical Formula

C₃₂H₄₀O₁₂

Average Mass

616.6600 Da

Monoisotopic Mass

616.25198 Da

IUPAC Name

(1S,2R,4S,7R,8S,10S,11R,12R,13S,18R,20R)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icosan-10-yl acetate

Traditional Name

(1S,2R,4S,7R,8S,10S,11R,12R,13S,18R,20R)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icosan-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]23[C@]2(C)[C@@H](C[C@@H]3[C@@](C)([C@@H]12)[C@H](CC(=O)OC3(C)C)OC(C)=O)OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C32H40O12/c1-15(33)39-19-13-29(6)25(18-9-10-38-14-18)42-27(37)26-32(29,44-26)31(8)22(41-17(3)35)11-20-28(4,5)43-23(36)12-21(40-16(2)34)30(20,7)24(19)31/h9-10,14,19-22,24-26H,11-13H2,1-8H3/t19-,20-,21-,22+,24+,25-,26+,29-,30+,31+,32+/m0/s1

InChI Key

LLKSEVKQBGUFFZ-DMULSHIBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cedrela odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Caprolactone
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxepane
Pyran
Oxane
Furan
Heteroaromatic compound
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.03	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	157.17 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.32 m³·mol⁻¹	ChemAxon
Polarizability	61.22 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58826807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101362571

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate (NP0318887)

MOL for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

3D MOL for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

3D SDF for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

3D-SDF for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

PDB for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

3D PDB for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

SMILES for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

INCHI for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

Structure for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)

3D Structure for NP0318887 ((1s,2r,4s,7s,8s,10s,11r,12r,13s,18r,20r)-13,20-bis(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-10-yl acetate)